Welcome back to our 2025 Red Sox Postmortem. After talking about the things we loved and hated, grading Craig Breslow and Alex Cora, reevaluating the Rafael Devers trade, handing out individual awards,
and assessing whether the season was a success, today we turn our attention of the offseason.
What should be Craig Breslow’s top offseason priority?
Acquiring a #2 starting pitcher. He can do so in free agency but will probably have to commit to keeping a guy until he’s at least 36. Trading? Well, there’s an outfielder who can be moved. And maybe one of Tolle or Early or Harrison if you think you can get, I don’t know, one step down from Garrett Crochet? A mid-20s non-ace but very very good starting pitcher. Otherwise it’s probably worth seeing if any of those three can just develop into that number 2 by 2027 and hope they’re ready in the second half instead?
—Mike Carlucci
Adding a significant power threat to the middle of the lineup, preferably from the right side. Unless that man’s name is Kyle Schwarber, in which case the left side will be just fine.
— Bob Osgood
A number two starting pitcher. Much fracas was made at the buzzer of the deadline about acquiring any of Joe Ryan, Merrill Kelly, Sandy Alcantara, someone who’d supplement the rotation so that in a three-game series, Connelly Early wasn’t trotting out there. And lo and behold, that’s exactly what happened. I like Brayan Bello and think he’s made tons of strides in becoming a formidable rotation piece for the duration of his career in just one year, and it’s even greater that he’s a homegrown talent, but I’m iffy to see him as a number two option. Now that it’s the offseason and these Joe Ryan types of arms aren’t at as much of a premium to contending teams, it might be time to kick the tires on that caliber of pitcher.
— Dean Roussel
Did you see what the Dodgers just did to the Brewers in Milwaukee with Blake Snell and Yoshinobu Yamamoto? The Red Sox have half of that in Garrett Crochet. Now they need to get something close to resembling the other half. Unfortunately, that’s going to require a trade because I don’t see any arm on the free agent market this winter that can fill the void.
— Matt Gross
If you have two horses at the top of your rotation, you barely even need to pay attention to the rest of the roster. Okay, that’s not entirely true, but it’s true-ish. There are whispers of Hunter Greene being on the trading block. He would cost a fortune, but he’d be worth every penny of a prospect package.
— Dan Secatore
Which pending free agent would you love to see on the 2026 Red Sox?
Last year was really the winter to sign a free agent pitcher. There are only two free agent starting pitchers under 30 years old. Their names: Dustin May and Michael Soroka. They’re weren’t exactly great this year or in their careers. There’s not a real reason to think Shane Bieber (31), Dylan Cease (30), Jack Flaherty (30) are worth breaking the “no 30+ starters on long-term deals” rule so it’s Bo Bichette or bust. And then, that’s really only if Trevor Story opts out.
—Mike Carlucci
Pete Alonso. I thought that he should’ve been a target of Boston’s a year ago, and after opting out of what amounted to a one-year, $30-million deal, combined with yet another Triston Casas injury, nothing has changed for me. Alonso’s defense leaves something to be desired, but I think he would wear out the Green Monster and be the threat that the team was lacking in the second half, after trading Rafael Devers.
— Bob Osgood
Bo Bichette. If Alex Bregman does not get offered a long-term deal, and/or if Trevor Story opts out, I have an easier time seeing Marcelo Mayer as a third baseman post-Devers departure than as a shortstop. That opens up the door to threaten the division winner from 2025 by taking one of their premiere players. Bichette, who’s going to be 28, ranked ninth in shortstop WAR and, aside from 2024, has consistently hit .300 or north for much of his career. Of course, there’s the issue of Bichette being a liability defensively, too, which is my lone reason to not pursue what would need to be a long-term deal.
— Dean Roussel
Assuming he opts out, Alex Bregman. It’s going to be an overpay, and the contract will become a negative asset on the backend, but it’s worth the price if he’s part of the DNA that helps establish a run of championship contention on the front end.
— Matt Gross
Bring me the Polar Bear.
— Dan Secatore
Should the Sox offer Alex Bregman a long-term (~five years) deal?
Sort answer: No.
Long answer: It depends. Five years at $40 million (or $30-something after deferrals or whatever) is a lot of the budget to dedicate to one player entering his normal decline period. But with the prospects coming up and relatively lower salaries, this isn’t the end of the world. But for a team that has tied one had behind its back dealing with players over 30 for the last decade, I really don’t understand breaking this rule for a guy who is solid but not a superstar.
— Mike Carlucci
Yes. Find a way to spread out that AAV since the team needs to get creative if they insist on not flying over the second luxury tax threshold, while still addressing all of their needs for 2026. Boston is the best fit for Bregman, and I believe that both the team and the player know that to be true.
— Bob Osgood
Yes, but see if there’s an avenue to an opt-out after three rather than four. I’d also be surprised to see a deal that has an AAV of more than 35, and the way money is spent years in advance and with how far that money could go, a player with his leadership fundamentals is hard to come by for that amount. There are enough young players guaranteed to be on the 2026 Red Sox that Bregman’s presence — and reliability — is needed to ensure a winning season.
— Dean Roussel
Yes, but unfortunately I think it’s going to take at least six years to ultimately get a deal done. This is going to become a saga that hangs over the offseason discussion like a black cloud and lasts for months.
— Matt Gross
If Trevor Story opts-out, should the Red Sox trigger their option to retain him through 2028?
If Craig Breslow and his team like Trevor Story, a Chaim Bloom holdover, yes. Because in this case it’s their choice. It’s the two years they expected to get plus one. If they don’t like Story, let him go, he was never the guy they wanted. Drive a dump truck full of money to Bo Bichette’s house, he’s not made of stone.
—Mike Carlucci
This one is tough because the Red Sox won’t know if Bregman will be returning via free agency (it’s nearly a certainty that Bregman opts out) when they make the Story decision. They’d be risking both Story and Bregman walking and would be without a 1B, SS, and 3B at the start of free agency. I think they have to pick up the 2028 option if it comes down to it.
— Bob Osgood
I would have never said this 12 months ago, but yeah, probably. When Story is hot, there’s no one better, and he’s also a much more solid defensive shortstop than others on the market with a net positive bat. If Bregman is going to play elsewhere, it’s a no-brainer.
— Dean Roussel
Yes, but it’s largely contingent on some of the other things I want the club to do. Ideally, the Red Sox will aggressively seek another high end starter, and in order to do that they’re probably going to have to get active in the trade market. This means you want to be dealing from a position of strength in the middle infield where Marcelo Mayer, Franklin Arias, and Mikey Romero are potential trade chips and not names carved in stone as needed replacements for Story’s departure.
— Matt Gross
Should the Red Sox trade one of their outfielders and, if so, which one?
Yes and it should be Jarren Duran which absolutely kills me to say. But Duran is best used in center field and Ceddanne Rafaela is even better there and it’s not particularly close. Is he the 2024 player or the guy we save in 2025 or someone in between? 2025 probably is the floor and if any team was willing to trade for Duran like his 2024 self he’d have been moved last winter for a starting pitcher.
—Mike Carlucci
Yes, especially if Kristian Campbell is going to transition to the outfield long-term. I would evaluate the market for both Wilyer Abreu and Jarren Duran and trade whichever has more value this offseason. If I had to guess, it’ll be Duran that goes.
— Bob Osgood
With Kristian Campbell not panning out in the infield, not even in Worcester, it’s probable the Red Sox will look to move Jarren Duran either Wilyer Abreu. The over-analyst in me would look for ways to keep everyone, as no one in the outfield was detrimental to the team. This includes conceding that Masataka Yoshida is the 2026 designated hitter and looking at ways that one of these players can log some innings at another position – Ceddanne Rafaela at shortstop, Jarren Duran at second. But then, it’s also more healthy for a team with so many defensive woes to optimize where everyone plays to where they won’t commit errors. Duran likely has some value in the open market, though, so I won’t be shocked if he’s the one that moves.
— Dean Roussel
Yes! Jarren Duran, Wilyer Abreu and Jhostynxon Garcia all need to be on the table as potential pieces in a deal that lands another high end arm. The only way somebody should answer “no” when asked if the Red Sox should trade one of their outfielders this winter is if their plan is to instead move two of them.
— Matt Gross
Yes. They should’ve done this last offseason, when Jaren Duran had a lot more value. As it is, I’d prefer he be the one to go out the door, but they should put all three on the table and take the best package they can get.
— Dan Secatore
